The nature of halogen substitution determines the mode of cytotoxicity of halopropanols

Toxicology and Applied Pharmacology

Volumn 155, Issue 3, 1999, Pages 287-291

  Hammond, Alison H ^a   Garle, Michael J ^a   Fry, Jeffrey R ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON TETRACHLORIDE; CYTOCHROME P450; GLUTATHIONE TRANSFERASE; HALOGEN; PROPANOL;

ANIMAL CELL; ARTICLE; BROMINATION; CYTOTOXICITY; FIBROBLAST; LIVER CELL CULTURE; LIVER INJURY; LIVER NECROSIS; LIVER TOXICITY; MICROSOME MEMBRANE; MOUSE; MUTAGENICITY; NONHUMAN; TOXICITY TESTING;

EID: 0033560127     PISSN: 0041008X     EISSN: None     Source Type: Journal    
DOI: 10.1006/taap.1998.8610     Document Type: Article

References (27)

1. Budavari, S. (Ed.). The Merck Index Merck, Rahway, NJ.
2. Borenfreund, E., and Puerner, J. A. (1986). Cytotoxicity of metals, metal-metal and metal-chelator combinations assayed in vitro. Toxicology 39, 121-134.
3. Chen, Q., Jones, T. W., Brown, P. C., and Stevens, J. L. (1990). The mechanism of cysteine conjugate cytotoxicity in renal epithelial cells. J. Biol. Chem. 265, 21603-21611.
4. de Groene, E. M., Hassing, I. G. A. M., Blom, M. J., Seinen, W., Fink-Gremmels, J., and Horbach, G. J. (1996). Development of human cytochrome P450-expressing cell-lines-application in mutagenicity testing of ochratoxin-A. Cancer Res. 56, 299-304.
5. Fry, J. R., Garle, M. J., and Lal, K. (1992). Differentiation of cytochrome P450 inducers on the basis of 7-alkoxycoumarin O-dealkylase activities. Xenobiotica 22, 211-215.
6. Garle, M. J., and Fry, J. R. (1989). Detection of reactive metabolites in vitro. Toxicology 54, 101-110.
7. Ghanayem, B. I., and Burka, L. T. (1987). Comparative metabolism and disposition of 1-chloro- and 3-chloro-2-methylpropene in rats and mice. Drug Metab. Dispos. 15, 91.
8. Hammond, A. H., and Fry, J. R. (1990). The in vivo induction of rat hepatic cytochrome P450-dependent enzyme activities and their maintenance in culture. Biochem. Pharmacol. 40, 637-642.
9. Hammond, A. H., and Fry, J. R. (1997). Involvement of cytochrome P4502E1 in the toxicity of dichloropropanol to rat hepatocyte cultures. Toxicology 118, 171-179.
10. Hammond, A. H., Garle, M. J., and Fry, J. R. (1996). Toxicity of dichloropropanols in rat hepatocyte cultures. Environ. Toxicol. Pharmacol. 1, 39-43.
11. Haratake, J., Furuta, A., Iwasa, T., Wakasugi, C., and Imazu, K. (1993). Submassive hepatic necrosis induced by dichloropropanol. Liver 13, 123-129.
12. Hatayama, I., Yamada, Y., Tanaka, K., Ichihara, A., and Sato, K. (1991). Induction of glutathione S-transferase P-form in primary cultured rat hepatocytes by epidermal growth factor and insulin. Jpn. J. Cancer Res. 82, 807-814.
13. Kamath, S. A., and Anaith-Narayan, K. (1972). Interaction of calcium with endoplasmic reticulum of rat liver: A standardised procedure for the isolation of rat liver microsomes. Anal. Biochem. 48, 53-61.
14. Khan, S., Sood, C., and O'Brien, P. J. (1993). Molecular mechanisms of dibromoalkane cytotoxicity in isolated rat hepatocytes. Biochem. Pharmacol. 45, 439-447.
15. McMillan, J. M., Shaddock, J. G., Casciano, D. A., Arlotto, M. P., and Leakey, J. E. A. (1991). Differential stability of drug-metabolising enzyme activities in primary rat hepatocytes, cultured in the absence of presence of dexamethasone. Mutat. Res. 249, 81-92.
16. Mico, B. A., Federowicz, D. A., Ripple, M. G., and Kerns, W. (1988). In vivo inhibition of oxidative drug metabolism by, and acute toxicity of, 1-aminobenzotriazole (ABT). A tool for biochemical toxicology. Biochem. Pharmacol. 37, 2515-2519.
17. Monks, T. J., and Lau, S. S. (1988). Reactive intermediates and their toxicological significance. Toxicology 52, 1-53.
18. Ortiz de Montellano, P. R., and Costa, A. K. (1986). Dissociation of cytochrome P450 inactivation and induction. Arch. Biochem. Biophys. 251, 514-524.
19. Pegram, R. A., Andersen, M. E., Warren, S. H., Ross, T. M., and Claxton, L. D. (1997). Glutathione S-transferase-mediated mutagenicity of trihalomethanes in Salmonella typhimurium: Contrasting results with bromochloromethane and chloroform. Toxicol. Appl. Pharmacol. 144, 183-188.
20. Recknagel, R. O., Glende Jnr, E. A., Dolak, J. A., and Waller, R. L. (1989). Mechanisms of carbon tetrachloride toxicity. Pharmacol. Ther. 43, 139-154.
21. Ridgewell, R. E., and Abdel-Monem, M. M. (1987). Stereochemical aspects of the glutathione S-transferase-catalysed conjugations of alkyl halides. Drug Metab. Dispos. 15, 82.
22. Rogiers, V., Vandenberghe, Y., Callaerts, A., Verleye, G., Cornet, M., Mertens, K., Sonck, W., and Vercruysse, A. (1990). Phase I and phase II xenobiotic biotransformation in cultures and co-cultures of adult rat hepatocytes. Biochem. Pharmacol. 40, 1701-1706.
23. Schrenk, D., Eisenmann-Tappe, I., Gebhardt, R., Mayer, D., El Mouelhi, M., Rohrdanz, E., Munzel, P., and Bock, K. W. (1991). Drug metabolizing enzyme activities in rat liver epithelial cell lines, hepatocytes and bile duct cells. Biochem. Pharmacol. 41, 1751-1757.
24. Shiozaki, T., Mizobata, Y., Sugimoto, H., Yoshioka, T., and Sugimoto, T. (1994). Fulminant hepatitis following exposure to dichlorohydrin - report of two cases. Hum. Exp. Toxicol. 13, 267-270.
25. Snyder, R., and Andrews, L. S. (1996). Toxic effects of solvents and vapours. In Casarett and Doull's Toxicology: The Basic Science of Poisons (C. D. Klaassen Ed.), pp. 737-771. McGraw-Hill, New York.
26. Thier, R., Muller, M., Taylor, J. B., Pemble, S. E., Ketterer, B., and Guengerich, F. P. (1995). Enhancement of bacterial mutagenicity of bifunctional alkylating agents by expression of mammalian glutathione-S-transferase. Chem. Res. Toxicol 8, 465-472.
27. van Bladeren, P. J., Breimer, D. D., Rotteveel-Smijs, G. M. T., de Knijff, P., Mohn, G. R., van Meeteren-Walchli, B., Buijs, W., and van der Gen, A. (1981). The relation between the structure of vicinal dihalogen compounds and their mutagenic activation via conjugation to glutathione. Carcinogenesis 2, 499-505.